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Norgestimate, sold under the brand names Ortho Tri-Cyclen and Previfem among others, is a progestin medication which is used in birth control pills for women and in menopausal hormone therapy.
Side effects of the combination of an estrogen and norgestimate include menstrual irregularities, headaches, nausea, abdominal pain, breast tenderness, mood changes, and others.
Norgestimate was introduced for medical use, specifically in birth control pills, in 1986.
Contents
1 Medical uses
1.1 Available forms
2 Contraindications
3 Side effects
4 Overdose
5 Interactions
6 Pharmacology
6.1 Pharmacodynamics
6.1.1 Progestogenic activity
6.1.2 Androgenic activity
6.1.3 Other activities
6.2 Pharmacokinetics
7 Chemistry
8 History
9 Society and culture
9.1 Generic names
9.2 Brand names
9.3 Availability
10 Research
11 References
12 Further reading
Medical uses
Norgestimate is used in hormonal contraception and in menopausal hormone therapy for the treatment of menopausal symptoms.
Available forms
Norgestimate is available only in combination with the estrogens ethinylestradiol and estradiol.
Contraindications
See also: Progestin § Contraindications
Side effects
See also: Norelgestromin § Side effects, and Progestin § Side effects
Norgestimate has mostly been studied in combination with an estrogen, so the side effects of norgestimate specifically or on its own have not been well-defined.
Side effects associated with the combination of ethinylestradiol and norgestimate in premenopausal women, with greater than or equal to 2% incidence over up to 24 menstrual cycles, include headache / migraine (33%), abdominal/gastrointestinal pain (7.8%), vaginal infection (8.4%), vaginal discharge (6.8%), breast issues (including breast pain, discharge, and enlargement ) (6.3%), mood disorders (including depression and mood alterations) (5.0%), flatulence (3.2%), nervousness (2.9%), and rash (2.6%).
Side effects associated with the combination of estradiol and norgestimate in postmenopausal women, with greater than or equal to 5% incidence over one year, include headache (23%), upper respiratory tract infection (21%), breast pain (16%), back pain (12%), abdominal pain (12%), flu-like symptoms (11%), arthralgia (9%), vaginal bleeding (9%), dysmenorrhea (8%), sinusitis (8%), vaginitis (7%), pharyngitis (7%), fatigue (6%), pain (6%), nausea (6%), viral infection (6%), flatulence (5%), tooth disorder (5%), myalgia (5%), dizziness (5%), depression (5%), and coughing (5%).
Overdose
See also: Progestin § Overdose
Interactions
See also: Progestin § Interactions
Pharmacology
Pharmacodynamics
Norelgestromin, also known as 17β-deacetylnorgestimate, the main active metabolite of norgestimate.
Norgestimate is a rapidly and completely converted prodrug, mainly of norelgestromin (17β-deacetylnorgestimate or levonorgestrel 3-oxime), but also of levonorgestrel (3-keto-17β-deacetylnorgestimate) to a lesser extent (22 ± 6% of an administered dose or about 40–70 µg)
Relative affinities (%) of norgestimate and metabolites
Compound
PR
AR
ER
GR
MR
SHBG
CBG
Norgestimate
15
0
0
1
0
0
0
Norelgestromin ( 17β-deAc-NGM )
10
0
?
?
?
0
?
Levonorgestrel ( 3-keto-17β-deAc-NGM )
150–162
45
0
1–8
17–75
50
0
Levonorgestrel 17β-acetate ( 3-keto-NGM )
135
?
0
?
?
0
?
Values are percentages (%). Reference ligands (100%) were promegestone for the PR, metribolone for the AR, E2 for the ER, DEXA for the GR, aldosterone for the MR, DHT for SHBG, and cortisol for CBG.
Progestogenic activity
Norgestimate is a progestogen, or an agonist of the progesterone receptor.
Androgenic activity
In addition to its progestogenic activity, norgestimate has weak androgenic activity.
The relative binding affinity of norgestimate and its metabolite norelgestromin for the rat prostatic androgen receptor (AR) are 0.3% and 1.3% of those of dihydrotestosterone (DHT), respectively, whereas the respective values for levonorgestrel and gestodene are 22% and 15%.
When norgestimate is combined with ethinylestradiol, which is potently antiandrogenic, there are only antiandrogenic effects overall and the combination is suitable for treatment of hyperandrogenism.
Other activities
Norgestimate and its active metabolites do not bind to other steroid hormone receptors besides the progesterone and androgen receptors and hence have no other off-target hormonal activity.
Pharmacokinetics
Norgestimate is rapidly and almost completely metabolized into its active metabolites, mainly norelgestromin (the primary active metabolite) and to a lesser extent levonorgestrel, upon oral ingestion.
Norgestimate is extensively metabolized into its active metabolites during first-pass metabolism in the liver and intestines.
Chemistry
See also: List of progestogens, Progestogen ester, and List of progestogen esters
Norgestimate, also known as 17α-ethynyl-18-methyl-19-nortestosterone 3-oxime 17β-acetate or as 17α-ethynyl-18-methylestr-4-en-17β-ol-3-one 3-oxime 17β-acetate, is a synthetic estrane steroid and a derivative of testosterone.
History
Norgestimate was introduced as a component of combined oral contraceptives in 1986.
Society and culture
Generic names
Norgestimate is the generic name of the drug and its INN, USAN, USP, BAN, and DCF.
Brand names
Norgestimate is marketed in combination with ethinylestradiol as a birth control pill under the brand names Amicette, Cilest, Cyclen, Edelsin, Effiprev, Estarylla, MonoNessa, Orlon, Ortho Tri-Cyclen, Ortho Tri-Cyclen Lo, Ortho-Cyclen, Pramino, Previfem, Sprintec, Triafemi, TriCilest, Tri-Cyclen, Tri-Cyclen LO, Tridette, Tri-Estarylla, Tri-Linyah, TriNessa, Tri-Previfem, and Tri-Sprintec.
Availability
Norgestimate in combination with ethinylestradiol is marketed widely throughout the world, including in the United States, Canada, the United Kingdom, Ireland, elsewhere throughout Europe, South Africa, Latin America, and Asia.
Research
A 2017 study found that norgestimate inhibits staphylococcal biofilm formation and resensitizes methicillin -resistant Staphylococcus aureus to β-lactam antibiotics.

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